(R)-4-(β-naphthyl)-1,3-dioxolane-2-one | 163351-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-4-(β-naphthyl)-1,3-dioxolane-2-one
• CAS: 163351-74-4
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: YRJNXEROLVCCMM-LBPRGKRZSA-N

物化性质

• 沸点：
  457.9±34.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-4-(β-naphthyl)-1,3-dioxolane-2-one 在 sodium azide 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-azido-2-(β-naphthyl)ethanol
  参考文献：
  名称：

  Enantioselective allylic oxidation of cycloalkenes by using Cu(II)-tris(oxazoline) complex as a catalyst

  摘要：

  Optically active copper(II)-tris(oxazoline) complex that was synthesized as a model compound of the active site of non-heme oxygenase, was found to catalyze allylic oxidation of cycloalkenes to give the corresponding 2-cycloalkenyl benzoates with moderate to excellent enantioselectivity (up to 93% ee) under the Kharash-Sosnovsky reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00322-0
• 作为产物：
  描述：

  2-乙烯基萘 在 sodium hydroxide 、 potassium osmate(VI) 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 生成 (R)-4-(β-naphthyl)-1,3-dioxolane-2-one
  参考文献：
  名称：

  Enantioselective allylic oxidation of cycloalkenes by using Cu(II)-tris(oxazoline) complex as a catalyst

  摘要：

  Optically active copper(II)-tris(oxazoline) complex that was synthesized as a model compound of the active site of non-heme oxygenase, was found to catalyze allylic oxidation of cycloalkenes to give the corresponding 2-cycloalkenyl benzoates with moderate to excellent enantioselectivity (up to 93% ee) under the Kharash-Sosnovsky reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00322-0

文献信息

• Nitrene‐Mediated C−H Oxygenation: Catalytic Enantioselective Formation of Five‐Membered Cyclic Organic Carbonates
  作者：Xin Nie、Chen‐Xi Ye、Sergei I. Ivlev、Eric Meggers

  DOI：10.1002/anie.202211971

  日期：2022.11.25

  A new strategy for the synthesis of non-racemic cyclic carbonates from abundant alcohol feedstocks is presented. The method exploits an unusual nitrene-mediated C−H oxygenation via a proposed 1,7-hydrogen atom transfer (HAT).

  提出了一种从丰富的酒精原料中合成非外消旋环状碳酸酯的新策略。该方法通过拟议的 1,7-氢原子转移 (HAT) 利用不寻常的氮烯介导的 C−H 氧化作用。
• Chemical Synthesis and Biological Evaluation of C-2 Taxoids
  作者：K. C. Nicolaou、J. Renaud、P. G. Nantermet、E. A. Couladouros、R. K. Guy、W. Wrasidlo

  DOI：10.1021/ja00114a005

  日期：1995.3

  An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.
• Nicolaou, Kyriacos Costa; Couladouros, E. A.; Nantermet, P. G., Angewandte Chemie, 1994, vol. 106, # 15/16, p. 1669 - 1671
  作者：Nicolaou, Kyriacos Costa、Couladouros, E. A.、Nantermet, P. G.、Renaud, J.、Guy, Rodney Kiplin、Wrasidlo, Wolfgang

  DOI：——

  日期：——